Sodium Hydroxide → 4-methyl-6H,7H-thieno[3,2-c]pyridine

To 5.70 g (0.0337 mol) of 2-acetylaminoethylthiophene (f-l) was added 157 ml of dry benzene; and while being refluxed, a mixture of 13.80 g (0.09 mol) of phosphorus oxychloride and 63 ml of dry benzene was added dropwise to the solution. After being refluxed for 2 hr., the mixture was cooled with ice, and the reaction solution was poured into 315 g of ice. Under ice-cooling, the mixture was adjusted to pH 10 or more with 48% aqueous NaOH, and the solution was extracted with ether. After being washed with saturated brine, the ether layer was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to give 4.45 g (Yield : 87.3%) of the objective product, 4-methyl-6, 7-dihydrothieno[3, 2-c]pyridine (g-l) as dark red liquid.

1. temperatureand while being refluxed
2. additionwas added dropwise to the solution
3. temperatureAfter being refluxed for 2 hr
4. temperature, the mixture was cooled with ice
5. temperatureUnder ice-cooling
6. extractionthe solution was extracted with ether
7. washAfter being washed with saturated brine
8. dry with materialthe ether layer was dried over anhydrous sodium sulfate
9. concentrationThe solvent was concentrated under reduced pressure

ORD record

ord-29007c3f6af24a5bbf723fd51d0f8d65

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04839365